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Chemical Structure| 3236-47-3 Chemical Structure| 3236-47-3
Chemical Structure| 3236-47-3

cis-1,4-Cyclohexanedimethanol

CAS No.: 3236-47-3

4.5 *For Research Use Only !

Cat. No.: A1308679 Purity: 95%

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Product Details of [ 3236-47-3 ]

CAS No. :3236-47-3
Formula : C8H16O2
M.W : 144.21
SMILES Code : OC[C@H]1CC[C@@H](CO)CC1
MDL No. :MFCD00064957
InChI Key :YIMQCDZDWXUDCA-UHFFFAOYSA-N
Pubchem ID :7735

Safety of [ 3236-47-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H319
Precautionary Statements:P264-P280-P305+P351+P338-P337+P313

Application In Synthesis of [ 3236-47-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 3236-47-3 ]

[ 3236-47-3 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 3399-22-2 ]
  • [ 3236-48-4 ]
  • [ 3236-47-3 ]
  • 2
  • [ 3399-21-1 ]
  • [ 3236-48-4 ]
  • [ 3236-47-3 ]
  • 3
  • [ 120-61-6 ]
  • [ 3236-48-4 ]
  • [ 3236-47-3 ]
  • 5
  • [ 1420954-46-6 ]
  • [ 3236-48-4 ]
  • [ 3236-47-3 ]
  • [ 34885-03-5 ]
YieldReaction ConditionsOperation in experiment
With CrO4(2-)*Ba(2+)*Cr2CuO4*CuO; hydrogen; at 250℃; under 212036.0 Torr; for 5h; DXCD (800 g of 83percent DXCD with balance MCHM and other impurities (1.7 moles of DXCD)) was hydrogenated at 4100 psi and 250°C with 40 g of CuCr catalyst for 5 hours. Approximately 95percent of the starting DXCD was converted to CHDM during this period as shown in the feed and product sample analyses in Table 2. In Table 2,the MCHM monoester of TPA is labeled "Monoester." Analyses were performed by gas chromatography and are shown as area percent.
  • 6
  • [ 95623-88-4 ]
  • [ 3236-48-4 ]
  • [ 3236-47-3 ]
  • 7
  • [ 1420954-46-6 ]
  • [ 3236-48-4 ]
  • [ 3236-47-3 ]
YieldReaction ConditionsOperation in experiment
With C16H30O; (4-methylcyclohexyl)methanol; at 225℃; under 258581.0 Torr; Hydrogenolysis of DXCD to CHDM - The product of the first hydrogenation shown in Table 3 was reacted further to produce CHDM. This reaction was performed continuously in a trickle bed reactor at 225°C and 344.7 bar gauge (5000 psig) using CuCr as a catalyst. Analyses were performed by gas chromatography and are shown as area percent. The analysis of typical product samples is shown in Table 5. [0119] The hydrogenolysis of DXCD produces two moles of MCHM for every mole of CHDM. The final product samples contain 12.9-13.1percent CHDM dissolved in MCHM. The product material contains lower concentrations of impurities than the feed material, largely due to the reduction of the MCHM ester. More than 90percent of the MCHM ester is reduced during the hydrogenolysis step, replacing some of the MCHM that was lost due to ether formation. The ether itself is relatively inert and would have to be removed in subsequent purification steps. Assuming that the area percent concentrations are equivalent to weight percent, the hydrogenolysis of DXCD was nearly 100percent selective to the formation of DMCD and no significant byproducts were observed during this step. The cis/trans isomer ratio of the CHDM product was 0.42.
With (4-methylcyclohexyl)methanol; hydrogen; at 250℃; under 212036.0 Torr; for 5h; DXCD (800 g of 83percent DXCD with balance MCHM and other impurities (1.7 moles of DXCD)) was hydrogenated at 4100 psi and 250°C with 40 g of CuCr catalyst for 5 hours. Approximately 95percent of the starting DXCD was converted to CHDM during this period as shown in the feed and product sample analyses in Table 2. In Table 2, the MCHM monoester of TPA is labeled ?Monoester.? Analyses were performed by gas chromatography and are shown as area percent.
With Pd/Al2O3; C16H30O; (4-methylcyclohexyl)methanol; at 225℃; under 259341.0 Torr; The product of the first hydrogenation shown in Table 3 was reacted further to produce CHDM. This reaction was performed continuously in a trickle bed reactor at 225°C and 344.7 bar gauge (5000 psig) using CuCr as a catalyst. Analyses were performed by gas chromatography and are shown as area percent. The analysis of typical product samples is shown in Table 5. [0119] The hydrogenolysis of DXCD produces two moles of MCHM for every mole of CHDM. The final product samples contain 12.9-13.1percent CHDM dissolved in MCHM. The product material contains lower concentrations of impurities than the feed material, largely due to the reduction of the MCHM ester. More than 90percent of the MCHM ester is reduced during the hydrogenolysis step, replacing some of the MCHM that was lost due to ether formation. The ether itself is relatively inert and would have to be removed in subsequent purification steps. Assuming that the area percent concentrations are equivalent to weight percent, the hydrogenolysis of DXCD was nearly 100percent selective to the formation of DMCD and no significant byproducts were observed during this step. The cis/trans isomer ratio of the CHDM product was 0.42.
  • 8
  • (3R,6S)-cyclohex-1-ene-3,6-dimethanol diacetate [ No CAS ]
  • [ 3236-48-4 ]
  • [ 3236-47-3 ]
  • 9
  • [ 107550-83-4 ]
  • [ 3236-48-4 ]
  • [ 3236-47-3 ]
  • 10
  • (3R,6S)-cyclohex-1-ene-1,4-dimethanol [ No CAS ]
  • [ 3236-48-4 ]
  • [ 3236-47-3 ]
YieldReaction ConditionsOperation in experiment
15.1%Chromat.; 78.6%Chromat. With hydrogen; In isopropyl alcohol; under 3345.86 Torr; for 20h;Autoclave; Example 9Preparation of cis- and trans-cyclohexane-1,4-dimethanolcis- and trans-Cyclohexane-1,4-dimethanol were prepared according to Equation 9. The ene diol (0.60 g, 4.22 mmol) dissolved in 42.2 mL of isopropanol (0.10 M) was added to a Parr bottle. Then 3.46 g of isopropanol-washed Raney Ni slurry was added. The bottle was placed into a Parr shaker. After purging with nitrogen, the bottle was pressurized to 50 psig with H2. The bottle was shaken for 20 hrs. After this time, the mixture was discharged from the bottle and filtered through a short plug of celite with an methanol rinse. The volatiles were removed under reduced pressure to reveal a colorless oil (0.52 g recovered). GC analysis: 78.6percent cis-CHDM, 15.1percent trans-CHDM, 1.26percent cyclohexane dicarboxylic acid (CHDA), and 5.04percent unknown. 1H NMR delta (CDCl3): 3.55 (bs, 4H), 2.07-0.86 (m, 10H).
  • 11
  • (1R,4S)-cyclohexane-1,4-dimethanol diacetate [ No CAS ]
  • [ 3236-48-4 ]
  • [ 3236-47-3 ]
YieldReaction ConditionsOperation in experiment
0.44%Spectr.; 82.3%Spectr. With potassium carbonate; In methanol; at 20℃; for 17h; Example 16Preparation of cis-1,4-cyclohexanedimethanol by hydrolysis of its diacetatecis-1,4-Cyclohexanedimethanol was prepared according to Equation 16. The diacetate (2.28 g, 9.99 mmol) was dissolved in 100 mL of methanol (0.10 M). Potassium carbonate (3.04 g, 21.9 mmol) was added all at once. The mixture was stirred for 17 hours at ambient temperature. The volatiles were then removed under reduced pressure. Water (100 mL) was added to the crude mix. The aqueous phase was then extracted three times with 100 mL of ethyl acetate. The organic extracts were combined and dried with Na2SO4. After filtration, the volatiles were removed under reduced pressure to yield a colorless oil (1.02 g recovered). GC analysis: 82.3percent cis-CHDM, 0.44percent trans-CHDM, and 17.3percent unknown. 1H NMR delta (CDCl3): 3.57 (d, J=6.0 Hz, 4H), 1.71 (m, 2H), 1.61-1.29 (m, 8H).
  • 12
  • (1R,4S)-cyclohexane-1,4-dimethanol diacetate [ No CAS ]
  • [ 100-21-0 ]
  • [ 3236-48-4 ]
  • [ 3236-47-3 ]
YieldReaction ConditionsOperation in experiment
0.12%Chromat.; 0.48%Chromat.; 90.5%Chromat. With methanol; potassium carbonate; at 20℃; for 17h; Example 17Preparation of cis-1,4-cyclohexanedimethanol by hydrolysis of its diacetateThe diacetate product from Example 5 (1.08 g, 4.73 mmol) was dissolved in methanol (9.50 mL, 0.50 M). Potassium carbonate (1.44 g, 10.4 mmol) was added all at once. The mixture was stirred for 17 hours at ambient temperature. The volatiles were then removed under reduced pressure. Water (10 mL) was added to the crude mixture. The aqueous phase was extracted three times with 25 mL of ethyl acetate. The organic extracts were combined and dried with sodium sulfate. After filtration, the volatiles were removed under reduced pressure to yield a colorless oil (0.43 g recovered). GC analysis: 90.5percent cis-CHDM, 0.48percent trans-CHDM, 0.12percent terephthalic acid (TPA), and 8.9percent unknown. 1H NMR delta (CDCl3): 3.57 (d, J=6.0 Hz, 4H), 1.71 (m, 2H), 1.61-1.29 (m, 8H).
  • 13
  • [ 63621-97-6 ]
  • [ 3236-48-4 ]
  • [ 3236-47-3 ]
  • 14
  • [ 1119-43-3 ]
  • [ 3236-48-4 ]
  • [ 3236-47-3 ]
  • 15
  • ethyl 4-formylcyclohex-3-enecarboxylate [ No CAS ]
  • [ 190321-74-5 ]
  • [ 3236-48-4 ]
  • [ 3236-47-3 ]
 

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